In 1990, Wiles began to pursue an interest in film-making, working on the set of the film Mr. and Mrs. Bridge, filming on location in Kansas City. Not long after, the Stephen King tele-movie, Sometimes They Come Back, came to town and he worked on the crew as well as appearing in scenes as an extra. After forming some connections while working on these films, Wiles ventured to Los Angeles where he appeared in commercials before landing the lead in an after-school special. In 1994, he had a part in the Bon Jovi music video "Always". 1994 also gave him his first lead role, in the indie movie WindRunner, appearing with Margot Kidder and Russell Means. In 1995, Wiles made the first of 32 appearances in Beverly Hills, 90210 as Colin Robbins, a role which gained him some note in Hollywood. In 1999, Wiles garnered the role of Maurice 'Bosco' Boscorelli in the television drama Third Watch; he appeared in all six seasons of the show from 1999-2005.
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